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DOI: 10.1039/A804792H (Paper) Reference Section for: Chem. Commun., 1998, 2053-2054

Synthesis of fluorine-containing cyclic amino acid derivatives via ring closing olefin metathesis

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Sergey N. Osipov, Alexey F. Kolomiets, Christian Bruneau, Michel Picquet and Pierre H. Dixneuf

Abstract

New N-protected α-CF3 amino esters with two alkene chains (1,7-dienes 3 and 1,6-dienes 5) were reacted with the ring closing metathesis catalyst Ru[double bond, length half m-dash]CHPh(Cl)2(PCy3)2 to give the α-CF3 dehydropipecolinate and prolinate derivatives 6 and 7.

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  13. Satisfactory spectroscopic data and elemental analyses were obtained for compounds 3–7. Selected data for 6a:δH(CDCl3) 2.71 (m, 1 H, CH2), 2.92 (m, 1 H, CH2), 3.65 (m, 1 H, NCH2), 3.83 (m, 1 H, NCH2), 3.88 (s, 3 H, OCH3), 5.72 (m, 2 H, HC[double bond, length as m-dash]CH), 7.51(m, 3 H, Ph), 7.95 (m, 2 H, Ph); δF(CDCl3)–71.1 (s, 3 F, CF3). For 6c:δH(CDCl3) 1.52 [s, 9 H, (CH3)3], 2.77 (m, 2 H, CH2), 3.82 (m, 1 H, NCH2), 3.85 (s, 3 H, OCH3), 4.25 (m, 1 H, NCH2), 5.75–6.00 (br m, 2 H, HC[double bond, length as m-dash]CH); δF(CDCl3)–71.9 (s, 3 F, CF3). For 7a:δH(CDCl3) 3.89 (s, 3 H, OCH3), 4.07 (m, 1 H, CH2), 4.62 (m, 1 H, CH2), 5.63 (m, 1 H, HC[double bond, length as m-dash]CH), 6.22 (m, 1 H, HC[double bond, length as m-dash]CH), 7.51 (m, 3 H, Ph), 7.85 (m, 2 H, Ph); δF(CDCl3)–72.1 (s, 3 F, CF3). For 7b(two conformers): δH(CDCl3) 3.39 and 3.74 (2 s, 3 H, OMe), 4.27 (dm, 1 H, J 15.9, NCH2), 4.41–4.61 (m, 1 H, NCH2), 4.93–5.41 (m, 2 H, OCH2), 5.59–5.76 and 5.83–6.00 (2 m, 1 H, [double bond, length as m-dash]CH), 6.16–6.35 (m, 1 H, [double bond, length as m-dash]CH), 7.24–7.40 (m, 5 H, Ph); δF(CDCl3)–71.91, –71.89 (2 s, CF3).
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